SELECTIVITY OF NUCLEOPHILIC ADDITION TO AND SUBSTITUTION AT ISOTHIOCYANATOCARBONYL GROUP. REACTIONS OF 4-PENTINOYL- AND 2-(2-PROPINYL)-4-PENTINOYL ISOTHIOCYANATE WITH AMINES AND METHANOL
4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N=C=S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides.The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureasonly.Both isothiocyanates afford with methanol as a nucleophile axclusively the corresponding O-methyl monothiocarbamates.
Kutschy, Peter,Kristian, Pavol,Dzurilla, Milan,Koscik, Dusan,Nadaskay, Robert
p. 995 - 1005
(2007/10/02)
On a study of acetylene-carboxylic acids. Part 13. 2-Pyrrolone formation from substituted 4-pentynamides.
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SCHULTE,REISCH,HOBL
p. 687 - 693
(2007/10/07)
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